Polymer support oligonucleotide synthesis XVIII1.2): use ofβ-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product
Open Access
- 11 June 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 12 (11) , 4539-4557
- https://doi.org/10.1093/nar/12.11.4539
Abstract
Various 5′-0-N-protected deoxynucleoside-3′-0-β-cyanoethyl-N,N-dialkylamino-/N-morpholinophosphoramidites were prepared from β-cyanoethyl monochlorophosphoramidites of N,N-dimethylamine, N,N-diisopropylamine and N-morpholine. These active deoxynucleoside phosphites have successfully been used for oligodeoxy-nucleotide synthessis on controlled pore glass as polymer support and are very suitable for automated DNA-synthesis due to their stability in solution. The intermediate dichloro-β-cyanoethoxy-phosphine can easily be prepared free from any PCl3 contamination. The active monomers obtained from β-cyanoethyl monochloro N,N-diisopropylaminophosphoramidites are favoured. Cleavage of the oligonucleotide chain from the polymer support, N-deacylation and deprotection of β-cyanoethyl group from the phosphate triester moiety can be performed in one step with concentrated aqueous ammonia. Mixed oligodeoxynucleotides are characterized by the sequencing method of Maxam and Gilbert.Keywords
This publication has 12 references indexed in Scilit:
- [57] Sequencing end-labeled DNA with base-specific chemical cleavagesPublished by Elsevier ,2004
- Solid phase synthesis of polynucleotides. VIII. Synthesis of mixed oligodeoxyribonucleotides by the phosphotriester solid phase method1Nucleic Acids Research, 1983
- Synthesis of mixed oligodeoxyribonucleotides following the solid phase methodNucleic Acids Research, 1982
- Automated Synthesis of Gene FragmentsScience, 1981
- Synthesis of oligodeoxyribonucleotides on silica gel supportNucleic Acids Research, 1981
- Rapid synthesis of oligodeoxyribonucleotides. V. Further studies in solid phase synthesis of oligodeoxyribonucleotides through phosphotriester intermediates.1980
- DNA chain length markers and the influence of base composition on electrophoretic mobility of oligodeoxyribonucleotides in plyacrylamide-gelsNucleic Acids Research, 1979
- Studies on polynucleotides. 146. High-pressure liquid chromatography in polynucleotide synthesisBiochemistry, 1978
- Synthesis of thymidine oligonucleotides by phosphite triester intermediatesJournal of the American Chemical Society, 1976
- Nucleotide chemistry. XX. Phosphite coupling procedure for generating internucleotide linksJournal of the American Chemical Society, 1975